Question 1

Which reagent(s) would you use to convert CH3(CH2) 6CO2H to CH3(CH2) 6CH2OH?

Accepted Answer

A)  NaBH4/H2O
B)  LiAlH4/ether,then H3O+
C)  PCC/CH2Cl2
D)  Zn,H3O+
E)  H2,PtF) A) and B)
G) D) and E)

Question 2

A Grignard reagent will produce a secondary alcohol when reacted with ___.

Accepted Answer

any aldehy...

Question 3

The final product,E,in the following reaction sequence is,

Accepted Answer

A)  I
B)  II
C)  III
D)  IV
E)  VF) C) and D)
G) A) and B)

Question 4

PCC and CrO3 are both Cr(VI)reagents.However,PCC/CH2Cl2 is useful in oxidizing primary alcohols to aldehydes,while the analogous reaction with CrO3/H2SO4 will typically produce carboxylic acids.Why?

Accepted Answer

Both reagents first oxidize the alcohol ...

Question 5

Which of the following reactions would serve as a reasonable synthesis of the following racemic alcohol (2-phenyl-2-butanol) ?

Accepted Answer

A)  
B)   
C)   
D)  Two of these choices.
E)  All of these choices.F) C) and D)
G) All of the above

Question 6

Which of these transformations cannot be classified as a reduction?

Accepted Answer

A)  RCH2Cl  →	o→  RCH3
B)  RCH=CH2  →	o→  RCH2CH3
C)  RCOOH  →	o→  RCH2OH
D)   2Cl  	o  RCH3 
B)  RCH=CH2  	o  RCH2CH3 
C)  RCOOH  	o  RCH2OH 
D)     
E)  All of these are reductions. " class="answers-bank-image d-inline" rel="preload" >
E)  All of these are reductions. F) B) and E)
G) C) and E)

Question 7

The final product,D,in the following reaction sequence,  ,would be?

Accepted Answer

A)   
B)   
C)   
D)   
E)   F) C) and E)
G) C) and D)

Question 8

Which of the reagents listed below would efficiently accomplish the transformation of CH3CH2CH=CHCH2CH2CH2OH into CH3CH2CH=CHCH2CH2CHO?

Accepted Answer

A)  KMnO4,OH-
B)  CrO3 / H2SO4
C)  PCC in CH2Cl2
D)  (i) (COCl) 2,DMSO,-60 oC,(ii) Et3N
E)  Two of these choices.F) A) and B)
G) C) and D)

Question 9

Which of the reagents listed below would efficiently accomplish the transformation of ethyl-3-pentenoate into 3-penten-1-ol? 4; ii) H2O B) NaBH4,H2O C) H2,Pd D) Two of these choices. E) All of these choices." class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)  i) LiAlH4; ii) H2O
B)  NaBH4,H2O
C)  H2,Pd
D)  Two of these choices.
E)  All of these choices.F) A) and E)
G) A) and C)

Question 10

The final product,E,in the following reaction sequence is,

Accepted Answer

A)  I
B)  II
C)  III
D)  IV
E)  VF) D) and E)
G) A) and D)

Question 11

Which of these compounds cannot be used to prepare the corresponding Grignard reagent?

Accepted Answer

A)  CH3OCH2CH2CH2Br
B)  (CH3) 3CCl
C)  CH2=CHCH2Br
D)  (CH3) 2NCH2CH2Br
E)   3OCH2CH2CH2Br 
B)  (CH3) 3CCl 
C)  CH2=CHCH2Br 
D)  (CH3) 2NCH2CH2Br 
E)    " class="answers-bank-image d-inline" rel="preload" >F) A) and E)
G) A) and D)

Question 12

List the following compounds in order of increasing level of oxidation:

Accepted Answer

A)  I,II,III
B)  III,II,I
C)  II,I,III
D)  III,I,II
E)  I,III,IIF) C) and D)
G) A) and C)

Question 13

What is (are) the principal product(s) formed when 1 mol of ethylmagnesium bromide reacts with 1 mol of 3-(N-methylamino) cyclopentanone?

Accepted Answer

A)  I
B)  II
C)  III
D)  IV
E)  VF) B) and E)
G) B) and C)

Question 14

List the following compounds in order of increasing level of oxidation:

Accepted Answer

A)  I,II,III
B)  I,III,II
C)  II,I,III
D)  III,I,II
E)  III,II,IF) A) and D)
G) A) and B)

Question 15

Which of the reagents listed below would serve as the basis for a simple chemical test to distinguish between CH3CH=CHCH2OH and CH3CH2CH2CH2OH?

Accepted Answer

A)  CrO3 in H2SO4
B)  Cold conc.H2SO4
C)  Br2 in CCl4
D)  NaOH/H2O
E)  NaBH4F) A) and E)
G) A) and D)

Question 16

Reaction of an alkyllithium with a ketone produces,after acid work-up,a ___ alcohol.

Accepted Answer

The answer of Reaction of an alkyllithium with a ketone...

Question 17

Which of the reagents listed below would efficiently accomplish the transformation of CH3CH2C≡CCH2CH2CHO into CH3CH2C≡CCH2CH2CH2OH?

Accepted Answer

A)  KMnO4
B)  NaBH4
C)  Br2 in CCl4
D)  H2,Ni
E)  Two of these choices.F) A) and B)
G) B) and E)

Question 18

Upon reaction with a primary or secondary alcohol,the change in oxidation state of chromium ion in Jones reagent is from ___ to ___.

Accepted Answer

The answer of Upon reaction with a primary or secondary...

Question 19

Suggest a reasonable synthetic strategy for the synthesis of 1,4-pentanediol from 4-hydroxybutanal HOCH2CH2CH2CHO.

Accepted Answer

Question 20

Your task is to synthesize  through a Grignard synthesis.Which pairs of compounds listed below would you choose as starting materials?

Accepted Answer

A)   
B)   
C)   
D)  More than one of these choices.
E)  None of these choices.F) A) and B)
G) A) and C)

Exam 12: Alcohols From Carbonyl Compounds

Which reagent(s) would you use to convert CH3(CH2) 6CO2H to CH3(CH2) 6CH2OH?

Correct AnswerverifiedShow Answer

Which of the reagents listed below would serve as the basis for a simple chemical test to distinguish between CH3CH=CHCH2OH and CH3CH2CH2CH2OH?

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The final product,E,in the following reaction sequence is,

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Which of the reagents listed below would efficiently accomplish the transformation of ethyl-3-pentenoate into 3-penten-1-ol?

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Which of the reagents listed below would efficiently accomplish the transformation of CH3CH2C≡CCH2CH2CHO into CH3CH2C≡CCH2CH2CH2OH?

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List the following compounds in order of increasing level of oxidation:

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List the following compounds in order of increasing level of oxidation:

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The final product,E,in the following reaction sequence is,

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A Grignard reagent will produce a secondary alcohol when reacted with ___.

Correct Answerverifiedany aldehy...View AnswerShow Answer

PCC and CrO3 are both Cr(VI)reagents.However,PCC/CH2Cl2 is useful in oxidizing primary alcohols to aldehydes,while the analogous reaction with CrO3/H2SO4 will typically produce carboxylic acids.Why?

Correct AnswerverifiedBoth reagents first oxidize the alcohol ...View AnswerShow Answer

Your task is to synthesize through a Grignard synthesis.Which pairs of compounds listed below would you choose as starting materials?

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Which of these compounds cannot be used to prepare the corresponding Grignard reagent?

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Which of these transformations cannot be classified as a reduction?

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What is (are) the principal product(s) formed when 1 mol of ethylmagnesium bromide reacts with 1 mol of 3-(N-methylamino) cyclopentanone?

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Suggest a reasonable synthetic strategy for the synthesis of 1,4-pentanediol from 4-hydroxybutanal HOCH2CH2CH2CHO.

Correct AnswerverifiedShow Answer

Reaction of an alkyllithium with a ketone produces,after acid work-up,a ___ alcohol.

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Which of the reagents listed below would efficiently accomplish the transformation of CH3CH2CH=CHCH2CH2CH2OH into CH3CH2CH=CHCH2CH2CHO?

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Which of the following reactions would serve as a reasonable synthesis of the following racemic alcohol (2-phenyl-2-butanol) ?

Correct AnswerverifiedShow Answer

The final product,D,in the following reaction sequence, ,would be?

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Upon reaction with a primary or secondary alcohol,the change in oxidation state of chromium ion in Jones reagent is from ___ to ___.

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Which reagent(s) would you use to convert CH₃(CH₂) ₆CO₂H to CH₃(CH₂) ₆CH₂OH?

Correct Answer
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Which of the reagents listed below would serve as the basis for a simple chemical test to distinguish between CH₃CH=CHCH₂OH and CH₃CH₂CH₂CH₂OH?

Correct Answer
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Which of the reagents listed below would efficiently accomplish the transformation of CH₃CH₂C≡CCH₂CH₂CHO into CH₃CH₂C≡CCH₂CH₂CH₂OH?

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any aldehy...
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PCC and CrO₃ are both Cr(VI)reagents.However,PCC/CH₂Cl₂ is useful in oxidizing primary alcohols to aldehydes,while the analogous reaction with CrO₃/H₂SO₄ will typically produce carboxylic acids.Why?

Correct Answer
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Both reagents first oxidize the alcohol ...
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Suggest a reasonable synthetic strategy for the synthesis of 1,4-pentanediol from 4-hydroxybutanal HOCH₂CH₂CH₂CHO.

Correct Answer
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Correct Answer
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Which of the reagents listed below would efficiently accomplish the transformation of CH₃CH₂CH=CHCH₂CH₂CH₂OH into CH₃CH₂CH=CHCH₂CH₂CHO?

Correct Answer
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Upon reaction with a primary or secondary alcohol,the change in oxidation state of chromium ion in Jones reagent is from _ to _.

Correct Answer
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